A Facile Access to Pyrroles from Amino Acids via an Aza-Wacker Cyclization

A facile and efficient synthesis of pyrroles from readily available amino acids is described. The key step in the method is an aza-Wacker oxidative cyclization catalyzed by palladium(II)/Cu(OTf)2. A series of pyrroles were obtained by this method under mild conditions.

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Bibliographic Details
Published inJournal of organic chemistry Vol. 73; no. 13; pp. 5180 - 5182
Main Authors Zhang, Zuhui, Zhang, Jintang, Tan, Jiajing, Wang, Zhiyong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.07.2008
Amer Chemical Soc
Subjects
Amino Acids - chemistry
Chemistry
Chemistry, Organic
Cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Kinetics and mechanisms
Molecular Structure
Organic chemistry
Physical Sciences
Preparations and properties
Pyrroles - chemical synthesis
Reactivity and mechanisms
Science & Technology
PALLADIUM
VITAMIN-E
HETEROCYCLES
HIGHLY SUBSTITUTED PYRROLES
REGIOSELECTIVE SYNTHESIS
EFFICIENT SYNTHESIS
CHEMISTRY
OXIDATIVE CYCLIZATION
FUNCTIONALIZED PYRROLES
INDOLES
Copper II
Catalytic reaction
Cyclization
Mild operating conditions
Nitrogen heterocycle
Palladium II
Aminoacid
Reaction mechanism
Oxidation
Chemical synthesis
Pyrrole derivatives
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Summary:A facile and efficient synthesis of pyrroles from readily available amino acids is described. The key step in the method is an aza-Wacker oxidative cyclization catalyzed by palladium(II)/Cu(OTf)2. A series of pyrroles were obtained by this method under mild conditions.
Bibliography:ark:/67375/TPS-KVS2ZLG7-3
istex:5C495030701C9EC690DBD2EC59022ED9D35664B6
Preparation of starting materials and characterization data for products. This material is available free of charge via the Internet at http://pubs.acs.org.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo800433b